1. Field of the Invention
This invention deals with compounds that combine either a precursor to a cycloaliphatic epoxide, a lactone, and an acrylate or a cycloaliphatic epoxide, a lactone, and an acrylate to form novel compounds that are useful as intermediates in various ways including coatings, inks, adhesives, sealants, shaped articles, and other end uses.
2. Description of the Prior Art
Cycloaliphatic epoxides, poly-e-caprolactone polyols, and acrylates are all known materials that are useful in the arts of coatings, inks, adhesives, sealants, and forming shaped articles. Cycloaliphatic epoxides and acrylates are useful, for example, in making products with high performance characteristics that can withstand weathering. Poly-n-caprolactone polyols are known to provide flexibility and/or toughness to a variety of products. The products are usually formed by opening of the oxirane ring on the cycloaliphatic epoxide, by reaction of the ethylenic unsaturation in the acrylate, and by reaction of the hydroxyl end-groups of the poly-e-caprolactone polyols.
Unsaturated polylactone derivatives of the following structural formula are known: ##STR1## wherein R.sub.1 through R.sub.8 are the same or different and are hydrogen, phenyl, or unsubstituted or substituted alkyl groups of 1 to about 8 carbon atoms, n has a value of one or two, R.sub.12 is hydrogen when n is one and does not exist when n is two, R.sub.9 through R.sub.11 are the same or different and are hydrogen, phenyl, or lower alkyl having 1 to about 5 carbon atoms with the proviso that not more than three of the R.sub.9 through R.sub.11 groups are alkyl or phenyl groups, m is an integer of from zero to about 12, and the average value of p has a value of from zero to about 30 or more. Also known are the 3,4-epoxides of such compounds and other derivatives prepared by coupling two of more of these molecules. Such compounds are disclosed in U.S. patent application Ser. No. 07/457,922, filed on Dec. 27, 1989, now abandoned, the disclosure of which is incorporated herein by reference.
Cyclohexenyl-alkyl and alkylcyclohexenyl-alkyl alcohol esters of .alpha.,.beta.-unsaturated acids as well as their homopolymers and copolymers are described in U.S. Pat. No. 3,536,687. The structural form of the monomer used was as follows: ##STR2## wherein R is hydrogen or methyl, G is alkyl and preferably lower alkyl having 1 to 4 carbon atoms, and G.sub.2 to G.sub.6 are hydrogen, alkyl, halogen, or alkoxy. These monomers were polymerized into soluble polymers that were used to make coatings. The coatings were oxidatively crosslinked in air and thus rendered insoluble.
(3,4-Epoxycyclohexyl)methyl acrylate and 3,4-epoxy-6-methylcyclohexyl)methyl acrylate have been described by Frostick and coworkers in J. American Chemical Soc., 81, 3350 (1959). Methacrylates of 3,4-epoxycyclohexanemethanols, which may be substituted with alkyl groups of up to 12 carbon atoms, especially with methyl in the 6-carbon position, are described in German Patent 1,063,808, Aug. 20, 1959 (Chemical Abstracts 55:14983e). These compounds were polymerized alone or together with olefinic compounds and subsequently hardened by reaction of the epoxide group.
Also known are compounds such as ##STR3## wherein R is hydrogen or methyl. These compounds are described in Japanese patent applications J01096177-A, published Apr. 14, 1989 (Chemical Abstracts 111(20):174832y) and J01186876-A, published Jul. 26, 1989 (Chemical Abstracts 112(8):56951j).
Japanese patent application 02018410, published Jan. 22, 1990 (Chemical Abstracts 112(24):218938q) describes the preparation of coatings for erasable white boards by curing siloxane methacrylates with (3,4-epoxycyclohexyl)methyl methacrylate. German Offenlegungsschrift DE-3807571, published Sep. 22, 1988 (Chemical Abstracts 110(10):77623c) deals with copolymers from the same monomers. German Offenlegungsschrift DE-3916035-A, published Nov. 30, 1989 (Chemical Abstracts 112(22):200731g) is a description of the reaction products of vinyl resins bearing acid groups and unsaturated alicyclic epoxides including (3,4-epoxycyclohexyl)methyl methacrylate. Copolymers containing (3,4-epoxycyclohexyl)methyl acrylate or methacrylate are described in a Japanese patent application J57047365-A, published Mar. 18, 1982 (Chemical Abstracts 97(6):40442e) as useful in thermosetting powder coating compositions.
However, not previously suggested or disclosed are the novel unsaturated polylactone acrylate, methacrylate, or ethacrylate derivatives and epoxidized polylactone acrylate, methacrylate, or ethacrylate derivatives of this invention, their derivatives, and their range of useful properties.